Reaktion #793319

Reaktionsgleichung

1-bromo-8-(4-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

copper(I) cyanide

→

title compound

Ausbeute 45.8%

1-Cyano-8-(4-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

Ausbeute 45.8%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for ten minutes before it
2. 2
   Sonstigequenched with water
3. 3
   Filtrationfiltered
4. 4
   WaschenThe organic layer was washed with water, brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigepurified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane

Vorschrift

A mixture of 1-bromo-8-(4-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (400 mg, 1.02 mmol) and copper(I) cyanide (183 mg, 2.04 mmol) in anhydrous dimethylformamide (4 mL) was refluxed for ten minutes before it was cooled to room temperature and quenched with water. The slurry was stirred with chloroform/isopropanol (3:1, 70 mL) and water for ten minutes and filtered. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane to give the title compound as a white solid (158 mg): MS: (+) m/z 339.07 (M+1).

Quelle